


A Leap of Faith

by tweetiebird



Category: Once Upon a Time (TV)
Genre: Alive!Liam, Alternate Universe, Alternate Universe - Modern Setting, Concerts, Emma needs to let people in, F/M, If You Squint - Freeform, Killian is a singer, New Year's Eve, New Year's Kiss, New Years, New Years Concert, Romance, not really a kiss but it qualifies as one
Language: English
Status: In-Progress
Published: 2016-01-02
Updated: 2016-01-03
Packaged: 2018-05-11 02:22:44
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 5,869
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5610346
Author URL: https://archiveofourown.org/users/tweetiebird/pseuds/tweetiebird
Summary: <blockquote class="userstuff">
              <p>Emma Swan had no idea how her roommate and best friend Ruby roped her into going out during New Years. She was planning on a quiet evening of Netflix and eating ice cream, and once it turned 11:50 she would have turned on the TV to watch the ball drop in New York. But instead of pulling out her favorite blanket and snuggling into her comfy couch getting ready for a movie marathon, she was checking herself in the mirror to make sure her outfit was somewhat presentable to go to a concert. </p><p>A concert which she did not want to go to.</p>
            </blockquote>





	1. All right now baby

**Author's Note:**

> So I'm kinda late on this, but I really did just get the idea while watching Pitbull sing at Bayside two days ago (I stayed up editing this so it's the 2nd here). 
> 
> I just wrote this up yesterday and just finished editing, so please if you find any errors, please correct me.

**Notes for the Chapter:**

> *edited to say 2016 and not 2015 :)

Emma Swan had no idea how her roommate and best friend Ruby roped her into going out during New Years. She was planning on a quiet evening of Netflix and eating ice cream, and once it turned 11:50 she would have turned on the TV to watch the ball drop in New York. But instead of pulling out her favorite blanket and snuggling into her comfy couch getting ready for a movie marathon, she was checking herself in the mirror to make sure her outfit was somewhat presentable to go to a concert. A concert which she did not want to go to.

Ever since Emma was small she hated going to concerts - outside or inside - they always get too crowded and stuffy and loud. Last time she went to a concert, a drunk man even tried to dance with her and he ended up falling asleep right on her foot. Nope not the best luck.

“Why do we have to go today?” Emma grumbled, pulling on her red leather jacket. She slid her combat boots on over her socked feet and patted down her leggings, once again checking to see if her outfit was ‘concert worthy’ as Ruby put it. Her golden hair was piled neatly on top of her head with some loose curls framing her face.

“Come on Emma, these guys are famous!” Ruby stated, bringing her hands into her chest in a prayer way, “They’re playing here in Boston because they were personally invited, and this is their home town! We can’t miss this!”

Ruby was wearing a deep red lacy dress with black pumps and a leather jacket. Her hair was let loose around her face. She was practically bouncing in place at the very thought of going to the concert.

“I think we can live without seeing them,” Emma sighed, dropping her pepper spray into her purse, just as a precaution to what Ruby had mentioned earlier about thieves and such. “What's their name again?”

“The Jolly Rogers of course!” Ruby exclaimed, beaming at the very thought of seeing them in person. “I even got front row tickets! This is a score and you will thank me for taking you, believe me.”

“We’ll see when we get there.” Emma said, rolling her eyes. She grabbed the tickets Ruby had set out on the counter because she was sure Ruby would forget them in her excitement, and together they headed out into the Boston streets, walking in the direction of the outdoor concert.

\---

Emma shifted uncomfortably in the crowd of people, trying not to bump any shoulders. Ruby was right - they did get front row seats. Right smack dab in the center of the stage too. People kept bumping into Emma, making her shift her weight between her left and right. More and more people flooded into the barricaded area, and those who could not fit were sent to the outskirts of the fencing. Just when Emma thought there wasn’t enough room to fit more people, another wave of humans came stomping in.

“I didn’t realize Boston had so many people!” She stated, leaning over to Ruby.

Ruby shrugged, “Hey I’m going to go grab a drink, want something?”

“Anything that’s refreshing,” Emma said right when Ruby turned to head out of the crowd. Emma looked over the swarm, seeing now why Ruby had gotten front row tickets - there weren’t that many people allowed into the front rows. Sure it was enough to push and bump her around, but all the way in the back people were practically getting trampled on. Many people were on top of shoulders, just trying to get a good view of the stage.

“Thank you,” Emma heard Ruby say behind her. She turned around to see Ruby had picked up a guard and had him escort her to her spot.

“How in the world did you get him to bring you here?” Emma implored, looking back in wonder as the man weaved his way through the crowd once more.

“Well you know, I’ve got my ways,” Ruby answered, taking a sip of her fancy martini. “Here.”

“Thanks,” Emma said, grabbing her beer. Just when she said that, a large black curtain was dropped from the top of the iron wielding, shielding the stage from view. The crowed erupted in cheers as light danced across the dark canvas.

“Its starting!” Ruby explained happily, jumping in place. The crowd quieted down as soft vibrations ripped through the swarm of people. Suddenly, the curtain dropped, revealing the band. Directly in front of Emma, was the lead (Killian something or other - her mind supplied). He wore a sinfully deep V neck shirt that clung to his sides, tight dark jeans, and an even darker leather jacket. His eyes were unnaturally blue as the shone in anticipation of the new year.

The singer ran his left hand through his dark shaggy hair, but that just made it stick up at every angle. “Good evening Boston, are you ready for the New Year?” Killian questioned, raising an eyebrow and a flashing grin. The mass of people erupted in a new wave of noise as he turned back to his crew, and with a nod, the clapping started. “Now, to start of the night, how about something nice for my old town yeah?”

The singer bounced in place before going into the song. Emma honestly had no idea what she was expecting - but the smooth and clear voice that washed over her definitely wasn’t it.

“So this is what you meant, when you said that you were spent...”

By the time the song was halfway done, Emma was dancing and singing with Ruby. The singer’s deep, rich voice flowed through her just the same as the music did. “Now don’t you understand, that I’m not changing who I am!” Emma sang loudly along with the other hundred people who came.

The band sang a few more cover songs, but when all became silent, everyone looked onto the band with anticipation. The singer turned around on his heels, shedding his leather jacket to reveal a shirt that before cling to his sides, but now as he was covered in sweat, it tugged and cling even tighter now to him in a way that might as well have been illegal in five states. Someone from the back brought out an acoustic guitar which he accepted with a grin. With a nod from the drummer, he headed back to the microphone.

“Now, I know we still have quite a while until the fish drops, but I’d like you all to hear something,” he started, tuning the guitar, “When I was young and new to this country, I was downright terrified. But you all brought in a wee Irish lad into your town and gave him the same opportunities that you would an American lad or lass. So, for inviting me out to your New Year's celebration, I’d like you all to hear a little something me and the lads have been working on. It's a little different from what we were just playing, but it comes from our hearts and we hope you would take it into yours as well.”

The cheering started again as he strummed the guitar. “There she stood in the street, smiling from her head to her feet...”

Aside from his voice, his guitar, and the steady claps of the crowd, there was no other noise. This song was definitely different from the other songs that the band played before because it was much slower with the acoustic guitar rather than the whole band. Emma clapped her hands together, swaying gently with the crowd.

“All right now baby, it's all right now,” He sang, bright eyes now burning into hers, and hers only. She couldn’t look away from him even if the world depended on it - with his smooth singing and eyes now staring directly into hers. She only broke eye contact with him when Ruby nudged her in the side with her elbow.

“I won’t be saying ‘I told you so’ anytime soon, but I will accept an apology,” She said with a wicked smile, white canine teeth showing with the grin in stark contrast to her scarlet lips.

The song continued, and with a disappointed look Emma noticed Killian was now looking out and over the crowds and no longer at her. Once it ended, they went energetically into the second set, which was somehow more pumped up than the last one. Towards the fourth song, the band excused themselves for a short break.  
  
The stars have now come out as the sky grew darker, and the only lights out now were the camera flashes and the laser show. Some people even took out lighters and were waving them about in the air. If Emma was home right now, she would be binge watching some show on Netflix.

After the short break, the Jolly Rogers came out once more to relieve the secondary band (the White Rabbits) and they started up a song once more. Around 11:50, Killian stopped singing to look up into the sky. “Only 10 minutes now until 2017! We got time for, let's say five quick songs yeah?” He stated with a tilted grin.

Emma had no idea how she stood there jumping, dancing and singing for two hours without once complaining, then she looked down to the bottle of alcohol that Ruby kept bringing to her whenever she ran out. ‘Thank you liquid painkiller,’ Emma thought, taking another swig of her drink.

At the end of the fourth song, Killian took a look at his clock and with a smile he announced, “Ten, nine, eight...”

And so the entire crowd erupted with cheers, counting down with him. Everyone was so ready for 2016 to be over, and awaiting for 2017 to come in a matter of seconds. Once Emma yelled five, a hand appeared in front of her. She looked up to she the shining eyes of the singer on her, smirking and waiting for Emma to take his hand.

“Good luck!” Ruby said before pushing Emma forward. She took his hand and was pulled up onto the stage. Once steadied, she saw how the other members of the band gaped at them, but they quickly picked up their fallen jaws and looked up as they yelled one. At the count of one, the crowd boomed with cheers, couples kissed, children sang out, and families hugged. Now noticing that he still had a grip on her hand, she was about to move until he lifted her hand up to his lips.

“Happy New Year love,” Killian stated, looking at her over her hand. Emma stood there motionless, just staring at him as a deep red rose to her cheeks. He smiled once more at her before turning to the microphone once again.

“Happy New Years everyone!” Killian said into the mic, “Now it's about high time that me and the lads best rest up for tomorrow’s show. Thank you all for spending the last moments of the horror that was 2016 with us and the first of 2017. Now give it up for my dear friends, the talented White Rabbits, who will lead you into the New Year!” And with a brazen kiss to the crowd, he led Emma down the stage. But instead of letting go of her hand and apologizing, he led her through the maze of technical equipment, stagehands, and workers, and into a trailer. The trailer - Emma noted - was littered with makeup kits, clothes, and there were several duffel bags on the counters.

Once there he dropped her hand only to scratch behind his ear. Instead of offering to sign something or take a picture with her, he offered her a drink. “Um, would you like something to drink lass?” He asked, moving to open the small refrigerator.

“Oh, um, what do you have?” Emma asks, shifting awkwardly in the center of the room.

“Soft drinks of every kind, water, beer...” He replied, tilting his voice downward. “Oh, and you can take a seat anywhere you’d like.”

“Beer please,” She said, taking a seat on the blue sofa. He pulled out two beers and handed her one.

“Oh how rude of me,” He said suddenly, “My name is Jones, Killian Jones. Pleasure to me you miss...”

“Swan. Emma Swan,” She said, “But I already knew who you were. My friend Ru- Oh my goodness Ruby! I completely forgot about her!”

“Was she the girl dancing with you earlier?” Emma nodded. “I believe Scarlet is bringing her here now.”

“Oh, okay,” Emma said. now relaxing. She took a long drink of her beer, then suddenly there was a rapping at the door. It swung open to reveal a starstruck Ruby, who looked liable to faint at any given second. The rest of the band poured into the small trailer and Emma just realized that all four members must sleep in the same trailer.

The drummer was a small blond woman named Hunter - who was nicknamed Tinkerbell or Tink for short. Then there was Will Scarlet who was on bass and Eric who was on guitar. Then of course Killian Jones on vocals.

Ruby sat next to Emma, giving half hooded looks to all the male members of the band but they all were preoccupied with other things to notice. Killian brought a chair over to Emma, and the two began to talk about everything and anything that came to mind. Emma found that the conversation with Killian ran smoothly, with very little bumps. He was glad to answer all of Ruby’s questions on his rise in stardom, and he even told then the he might be staring in the cinema soon.

When he wasn’t busy being interrogated by Ruby - who insisted on getting a picture and video with him saying he loves her for her internet followers - he spent all the time that was allowed talking to Emma and learning about her. He asked about her work and she replied with short answered and quick statements. Emma still had no idea why she stayed there in the trailer for as long as she has because in the end, he will break her like everyone has. He’s the type that she’s been trying to avoid - the cocky, cheeky, possibly full of themselves type. The type that knows exactly what he does to her - but she can’t help but be pulled in.

“Little brother, I think it's way past your bedtime,” said a voice at the door. “Say goodbye to your little friends now.”

“Younger brother,” Killian sighed, but still got up. “Emma, Ruby, may I introduce my vexatious brother Liam, who is also the band manager and husband to our very own Lady Bell.”

As if summoned, the small blond woman appeared suddenly from their shared trailer room and tucked herself into Liam’s side with a smile.

“It's time to start packing up and heading out, the next place you guys were invited to play at is somewhere on the west side of Boston, so if we want to beat the New Year's traffic, we best be heading out now.” Liam informed, kissing the top of Tink’s head in greeting.

“Alright, alright.” Killian stated, reaching out a hand to help Emma up.

“Pleasure meeting you both, and I am sorry for cutting your chat with my little brother short but we do have to be heading out if they want to sleep in.” Liam said with an apologetic smile. The other band members heard this and from their one room they shouted their goodbyes and well wishes for the year.

“Younger brother,” Killian muttered before turning his attention to Emma, “And thank you again love for not fainting on me up there, anyone else I would have pulled would have gone limp on me.”

“You're very welcome Jones,” She replied, taking a drink of water that someone had brought out to her about 30 minutes ago. He showed Emma and Ruby out of the trailer and into the cold, dark Boston morning. The sun wasn’t out yet - it was far too early for that still - but the city was illuminated by cars, street lamps and people still up and celebrating the coming year.

“So,” Killian said once they got out. Reaching up to scratch behind his ear, he continued, “I’d very much like to see you again Swan, may I be honored with your telephone number?”

Emma stopped, staring back at him with wide eyes. She knew that seeing him might cause her to break, and she had to look of someone who wants to run. He noticed it and continued, “You know I once did nothing but run. I ran until I found a place I missed, a place to call home,” He patted the trailer side, “It's not much but it is home. Take a leap of faith Swan.”

She narrowed her eyes at him, but every sign she received told her he wasn’t lying. No red flags, no red herrings, just a nervous guy who seemed to honestly want her number. Emma tore her eyes from him and went through her purse, searching for the pen she always kept in there. Once she found it, she met him halfway on the steps, him slightly leaning downward and her slightly leaning up and into him. Emma held out her hand, waiting for him to reveal his arm, and once her did she scrawled her phone number onto his hand.

“There you go,” Emma stated, stepping back. “Don’t make me regret that Jones.”

“I don’t intend to,” He replied, smirk turning into a soft and pleasant smile, “Have a safe trip home, and a goodnight Swan. And it was a pleasure to meet you Ruby.”

“Oh please, the pleasure was all mine,” Ruby replied with a grin. She nodded to him before grabbing Emma’s arm and pulling her down the street.  
  
\---

Once Emma and Ruby turned the corner and were heading down their street, Emma decided to break the silence, “You can say it.”

“Say what?” Ruby questioned, feigning ignorance. She brought her red gloved hand to her cheek and even scrunched up her brows in order to make the point even clearer.

“You know what,” Emma sighed, swiping the card down the slot in order to open their building door.

“I told you so!” Ruby laughed, kicking off her heels once they got inside. She bent down and picked them up as they trudged up the stairs. “Oh and Emma, I heard your phone do that dingy thing it does.”

“How in the world did you hear that?” Emma asked, searching her purse for her cell. “It was on low.”

Emma pulled it out, only to find it had one new text from an unknown number. She swiped the screen, inputted her password, and opened the message box. When she read the new message, she let out a small but soft and bright smile. With a sigh, she put her phone down and headed off to bed. Today definitely turned out to be a trip, and she welcomed the next adventure that would surely come.

_Unknown: To my dear Swan, a goodnight and sleep tight is in order. I only wish you the best of dreams. Until you grace me with your lovely presence again. - Jones._

Yup, she definitely welcomed the adventure.


	2. I am a pirate, you are a princess

**Summary for the Chapter:**

> "You're a girl right?" Killian asked Tink.  
> She looked over to him and narrowed her eyes, "I should hope that fact was clear by now," She deadpanned.  
> "Help me please," He finally said after a long silence.

**Notes for the Chapter:**

> First half is Killian's pov, second half is Emma's. THIS IS OVER THE COURSE OF THE WEEK!!!
> 
> haha yes hello it's been a year but I'm back and I will get this done in real time (last chapter would be the New Year's chapter) because the holidays and everything will match up and be posted like so. 
> 
> Once again, it will be posted in real time (for example, the valentine's day chapter will be posted on valentines day), so I will try my best to keep up.
> 
> OKAY SO this chapter consists of two days (january 5th and 8th) because I don't want this fic to be that long (imagine a fic with over 200 chapters since this will be realtime [HA]). Despite this, the actual date will be updated on the said date - January 8th.

It took Killian exactly five and a half days to finally get his act together and call Emma in order to set a time for their date. With the traveling and performances, he's barely found time for himself, but he managed to squeeze in a few minutes alone in order to make that call (with the help of Tink and his brother of course). He had been so worried that she wouldn't want to see him - or worse, that she would be like another other girl he's gone out with - but she seemed to talk freely with him, and for that he was thankful. It wasn't often that people overlooked that fact that he was a famous singer and actually saw more than his wallet, but he was honestly thankful for whoever is watching over him that brought this lovely woman into his life that finally saw Killian and not the lead singer of the  _Jolly Rogers._

Of course he'd seen that same look to run that he knows oh so well, but she didn't run when he asked for her number. In fact she had put the ball in his park by giving him her number, letting him decide when to actually call. Then again it could have only been due to the vast amount of alcohol she had consumed and the fatigue that was getting to her that had driven Emma to disclosing her number to him, but he'd rather have an optimistic view of things. And an optimistic mindset he did have when he finally punched in Emma's digits into his phone and pressed call. 

"It's not good form to keep a lady waiting," Killian said through the phone once Emma answered, "And for that, I am terribly sorry love." 

" _Killian, hi._ " Emma's voice came clearly over the phone. She sounded tired and unrested, but Emma still made an effort to answer so that good was a good sign he thought.

"Good afternoon Swan," Killian stated with a wide grin that he knew she couldn't see. "How have you been?"

_"I've been good,"_ She mumbled. _"Deep to my throat in work though. Way too many cases during the holidays."_  
  
"I'm sorry about that love, but hopefully you'll feel better after a relaxing night out in town," Killian said, "Perhaps this Sunday at seven?"

" _As in a date?"_ Emma assumed.

"Only if you wanted it to be," Killian asserted, waving away the station manager who tried to talk to him. He ducked under a light and hid in the dark corner between two large iron masts and out of the sight of anyone who might try to disturb him.

_"Hmm I guess I can try to squeeze you in,"_   Emma said jokingly,  _"You know, so much to do nowadays, so little time."_

"Right you are Swan," Killian agreed, "So it's a date?"

_"Right you are Jones."_ Emma echoed. 

They talked a little bit afterwards until Killian could no longer put off the interview he had been avoiding. The station manager ran past him three times already shouting his name, so he figured it was time to stop hiding. Killian managed to get Emma to agree on letting him plan their night out and with some reluctance she gave him her address ( _You don't have to pick me up Jones, I have a car you know;_   Why don't you let me play the part of a gentleman Swan?). Their date was set for this Sunday at 7 - thankfully she had no obligations to go chase the common criminal that day and he had no prior band engagements - so it was all planned.

Well most of it anyway, now all he had to do was come up with a stunning night out for his lovely date, and he hoped to deliver.

"And now, we'd like to introduce our next guest stars. The hot new band: The Jolly Rogers!" Shouted the overzealous TV host.  _Time to make an appearance Jones._

\---

"What are you planning on doing?" Tink asked from her top bunk in the trailer as soon as Killian had strolled in. He was finally released from the TV interview - Killian was preoccupied with signing autographs for the children and grandchildren of the station's workers - and he was awfully tired. The other members of the band however were released beforehand _(the lucky sods)_ so they were all already comfy and getting ready for bed.

"Planning to do about what?" He replied, feigning ignorance. 

"Why your date after all," Eric answered when he came into the joint kitchen.

Tink swung her legs over the side of the bunk and jumped down gracefully in front of Killian. "Aw look Eric, he's smitten!"

"Smitten as a kitten," Will joked in a sing-song voice. 

"How did you know about that you pricks," Killian sighed as he pinched the bridge of his nose thinking _"Absolutely no privacy here."_

"We see all," Tink stated ominously, bugging out her eyes comically.

"She means we overheard your telephone conversation with Emma," Eric admitted, "Well we heard your half but from what we did hear we knew it went well."

"You following your wife's lead now McKinney?" Killian teased Eric with a raised brow. "Anyway to answer your previous inquiry Lady Bell, I'm planning on taking Emma out to dinner at my favourite restaurant and perhaps a stroll through the quiet Boston streets."

"How romantic!" Will drawled, grabbing Tink's hand and spinning her around. They dancing around a bit, putting on a silly performance for Eric and Killian, but Tink slapped his arm when Will finally let go of her. Tink waved her left hand at Will, plainly showing off her wedding band before she climbed up the small ladder to her bunk.   
  
"Shut it Scarlet," Killian barked. "I don't want her to be too overwhelmed and run on me."

"Thats a good plan," Tink agreed, falling back onto the bed. "Oh, and give her a single rose."

\---

Finally the day of the date arrived, and Killian was worried out of his wits. What if he came on too strong and she runs? What if he is a terrible conversation and she thought him to be vacuous? What if something goes terribly wrong and she ends up getting food poisoning? What if she doesn't like the place he's bringing her to?

_So much to do nowadays, so little time_. 

Liam and Tink walked in on Killian when he was practically throwing every article of clothing he had in his small trailer closet and onto his bunk. He made a mighty fine mountain of clothes when they finally thought it was time to help him.

"Little brother what in the world are you doing now?" Liam questioned, crossing his arms over his chest while Tink nodded next to him.

"I'm trying to find something to wear for tonight," Killian mumbled, along with a " _Younger_ brother,"

"See I told you he was  _smitten!"_ Tink laughed, looking up at Liam before going to the clothes pile and sorting through it.

Oh course, why didn't he think of it before? "You're a girl right?" Killian asked Tink.

Tink looked over to him and narrowed her eyes, "I should hope that fact was clear by now," she deadpanned.

"Help me, please," Killian finally said after a long silence. Killian knew that his sister-in-law would help him no matter what because they'd been good friends before her and Liam had gotten together, and even more so when she and his brother finally tied the knot. Still Killian didn't like to beg, but he knew that if he didn't, Tink would only pry it out of him one way or another - she thought of him as her helpless little brother after all.  

"Aw, all you had to do was ask Captain," She drawled, going back to the clothes pile. After rummaging through it, she pulled out a long sleeved navy blue shirt and his black vest. She then lifted the articles into the air with a wide grin, "Wear this. This is what you were wearing when _People_ put you in that 'Sexiest Man Alive' thing. Also find your skinny black jeans, those look good on you."  
  
"Are you sure?" Killian said, looking over the clothes Tink held in the air.

"You'll knock the poor lass right off her feet little brother," Liam stated, coming up behind Killian and patting his shoulder.

"I hope you're right,"

* * *

"He called," Emma exclaimed as soon as she walked into her apartment and saw Ruby. Killian had called her before she entered the restaurant that she was meeting the bounty she needed to apprehend. All went well until he became extremely defensive and attempted to run out. It all came through, she was able to inform the authorities and collect her income (but not after having wine thrown on her nice dress). She kicked her heels off and headed to the couch where Ruby was lounging.

"Care to be more specific?" Ruby asked without looking up from her magazine. 

"Killian called," Emma clarified, rolling her eyes. Who else would call? 

This certainly got Ruby's attention because she dropped her magazine and swung up in order to face Emma. "Is there a date? Please tell me there is a date because after what I saw, you two connected out there!"

"Yes there's a date." Emma sighed, picking up the magazine only to see a large spread of Killian Jones himself.

"When? Where? I need details!" Ruby practically shouted in her excitement. She pulled out her phone and started to type rapidly across the screen, "My followers are going to have a field day with this! They've already dubbed you two 'Captain Swan'!"

"Sunday at 7. I don't know where though," Emma replied. "Wait, why, and more importantly _how_  do your internet followers know about us? And why Captain Swan?" Emma did a double take, knowing full well just how many followers Ruby has on her social media outlets. 

"Because I took a picture when he kissed your hand, and another when you two were engrossed in your own little world in the trailer. You two are already all over the tabloids and the internet! And it's 'Captain Swan' because Killian Jones is known as the 'Captain' of the Jolly Rogers and I may have kinda disclosed your name on one of the posts I made of you a while back. Somehow someone went searching through my 'Life' tags and found your last name." 

This set Emma back, how in the  _world_ could she have appeared in the tabloids? Then again, she was pulled on stage by a gorgeous man who happens to be the lead singer in one of America's most known bands, not to mention on a televised New Year's event. Well it could have been worse - she could have fallen or accidentally given the world a view of something that the world most definitely has no business in seeing. Yeah, it could have been worse.

"Urg,"

"Why don't you know where?" 

"Killian said that he wanted it to be a surprise or something,"

"Aw that's romantic," 

"Yeah well you can tell him that when you see him on sunday," Emma suggested. "He insisted on picking me up."

"The apartment is in no condition to be seen by anyone but us!" Ruby shouted, springing up and rushing to pick scattered items off the ground.

"The dates in like three days, we have enough time to pick up,"

"Yeah but I want us to give off a 'we always keep the apartment cleaned no matter what day it is' feel."

"Whatever you say," Emma sighed and began to help her friend pick up. 

\---

Finally the big day arrived, and Emma was terrified. Many questions ranging from _what if he realizes that I don't fit in with his type of crowd_ and _what if I screw up_ ran wildly through her head. At this point she had no idea what to expect, and there was always the possible 'homicidal maniac date' to look out for - which was a main reason why she didn't normally go on dates to begin with. 

"I think you should go for the short red dress," Ruby said while rifling through her closet. Emma had enlisted her friend to help her get ready because she knew Ruby would want a say in this sort of thing. That and if she wore something that Ruby disapproved of, her friend would badger her until she gave in. Which happened more often than not.

"It's more your style," Emma exclaimed, taking in the short, strapless crimson dress her friend held out, "That and I'm pretty sure it _is_ yours." 

"You'd still look pretty fine in that dress though," Ruby stated, hanging it back in Emma's closet.

After about ten minutes, Emma was pretty sure they had gone through her entire wardrobe - after all she was never one to keep an item that she did not need - so Ruby had to go into her clothes stash in order to find something that she deemed presentable. After about five minutes, Ruby told Emma to turn around and wait.

"I dont know why I have to turn around," Emma complained, but still turned around.

"Just dont complain," Ruby said, pulling out a dress. "Now turn around!"

Ruby held out a cute, light peach dress with a V neckline. The dress looked as though it would reach her knees, and it also had a thin, peach colored belt around the waist. "I found this in the back of my closet, and seeing as we wear each others clothes all the time, you should have no trouble slipping this little ditty on."  
  
"Ruby, this is perfect," Emma stated, reaching out to feel the soft material the dress was made out of. "When did you get this?"

"Well Granny was upset in regards to my wardrobe choices," Ruby explained, gently setting the dress on Emma's bed, "And so she bought me this. I always wear it when she wants to go out with me. I'm pretty sure I have a pair of heels that would match this, let me go check." 

Ruby ambled out if the room, skipping along. Emma stared at the dress, with renewed confidence. If Ruby thinks this will go well, then it sure as hell would. And she'd make sure of that. Emma's been shying away from dates and commitment ever since what happened with Neal, and then Walsh. She didn't have a good experience with any major love interests, and with being in and out of the foster system so much, Emma decided it was better to put up walls.

When her parents first adopted her, they had a hard time breaking those walls. Becoming friends with Ruby helped her a lot with breaking a few down, but they never really disappeared. And now she had a chance to open herself up to another person - which of course may end with her walls being reinforced with steel.

_Take a leap of faith Swan._

"Found a pair!" Emma heard Ruby yell from her room. Great, now she would have to apologize to their neighbors for Ruby's loudness - again. 

Ruby came in and jumped on her bed, careful not to rumple the dress. She held out a pair of beautiful peach heels. "I hope these work,"

"They do!" Emma smiled, going around to hug her friend, who with a laugh and a smile of her own, hugged Emma back.

"Oh this is so exciting, with this you'll look like a princess!" Ruby stated, "You'll be the princess to his pirate, like in that one Playradioplay song, how romantic!"

"I think I'm the farthest thing from a princess," Emma laughed, "Now go, he's coming in about an hour and I'm still in my Star Wars PJs."

**Notes for the Chapter:**

> Any songs you guys think fit Captain Swan? If so mention them below! (It would be a great help to me because if you noticed the titles are a lyric from a song mentioned/ played in the chapter, so I need to hoard as many captain swan songs I can (please help)

**Author's Note:**

> Would anyone like to see this AU be expanded and not be a oneshot? If so drop me a comment telling me.
> 
> ***I do not own any of the songs mentioned here, and the two lines that Killian sing's that said the "Jolly Rogers" wrote, well doesn't belong to me either (I honestly did try to write a song but I couldn't). It's the song that Colin sang at a fan panel titled "All Right Now" by Free***
> 
> *Unbeta'd so if you see any mistakes, please correct me so I can fix them!  
> **If you liked this please drop a comment or kudo to show your support!


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